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- W2060017362 abstract "The preparation of 17β-substituted 14β-hydroxysteroid C-3 α-l-rhamnopyranosides is described. These derivatives have a 14β,20-ether, 14β,20-lactone, or 17β-CH2CH2OH, −CH2CH2NH2, −CHCHNO2(E), −CHCHCOOH(E), −CH(OH)CH2NO2(R), −CH(OMe)CH2NO2(R), −CH2CH2COOH, or −CH(OH)CH2NH2(R) group. Derivatives were assayed in a radioligand binding assay for [3H]ouabain in membranes from canine heart muscle. The digitalis “receptor” comprises isoenzymes of the ion-pumping enzyme, Na+,K+-ATPase. The 17β-CHCHNO2(E), 17β-CHCHCOOH(E), and 17β-CH(OMe)CH2NO2(R) derivatives were the most potent and equivalent to ouabain with low-nanomolar IC50 values. The very potent binding affinity of the disubstituted compound 17β-CH(OMe)CH2NO2(R) further demonstrates that 17β-unsaturated substitution is not required for potent binding affinity. This observation may be of value in the separation of cardiotonic and cardiotoxic effects. Tosylation of the 17β-CH2OH, prepared from the 17β-CHO by lithium aluminum hydride reduction, yielded the 14β,17β-ether. Synthesis of the 17β-CH2COOH gave the epimeric 14α,17α- and 14β,17β-lactones. Structures have been established by NMR analysis." @default.
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- W2060017362 date "1997-05-01" @default.
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- W2060017362 title "Synthesis and Structure−Activity Relationships of 17β-Substituted 14β-Hydroxysteroid 3-(α-<scp>l</scp>-Rhamnopyranoside)s: Steroids That Bind to the Digitalis Receptor" @default.
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- W2060017362 doi "https://doi.org/10.1021/jm960880l" @default.
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